Cheapest return flights from Chicago to San Juan in December from 301€

AirHint found the following cheapest return flights from Chicago (MDW) to San Juan (SJU) in December 2025 (see full year).

Return flights

24 Dec - 10 Jan Frontier Airlines
24 Dec - 27 Dec Frontier Airlines
24 Dec - 28 Dec Frontier Airlines
24 Dec - 26 Dec Frontier Airlines
25 Dec - 31 Dec Frontier Airlines
30 Dec - 02 Jan Frontier Airlines
27 Dec - 31 Dec Frontier Airlines
25 Dec - 01 Jan Frontier Airlines
27 Dec - 29 Dec Southwest Airlines
29 Dec - 01 Jan Frontier Airlines
27 Dec - 30 Dec Frontier Airlines
27 Dec - 01 Jan Frontier Airlines
22 Dec - 24 Dec Frontier Airlines
22 Dec - 10 Jan Frontier Airlines
25 Dec - 28 Dec Frontier Airlines
28 Dec - 06 Jan Frontier Airlines
26 Dec - 31 Dec Frontier Airlines
22 Dec - 06 Jan Frontier Airlines
29 Dec - 02 Jan Frontier Airlines
29 Dec - 04 Jan Frontier Airlines

Also check the deals for one-way flights from Chicago to San Juan in December.

Powered by

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

Book a cheap hotel in San Juan

Cheap car rent in San Juan

Feel free to contact us with any feedback or request another flight research.